KR20200052936A - 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 - Google Patents
과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 Download PDFInfo
- Publication number
- KR20200052936A KR20200052936A KR1020207010465A KR20207010465A KR20200052936A KR 20200052936 A KR20200052936 A KR 20200052936A KR 1020207010465 A KR1020207010465 A KR 1020207010465A KR 20207010465 A KR20207010465 A KR 20207010465A KR 20200052936 A KR20200052936 A KR 20200052936A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- mmol
- hyperglycemia
- optionally substituted
- mixture
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 73
- 201000001421 hyperglycemia Diseases 0.000 title claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 title description 20
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 312
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims description 160
- 238000000034 method Methods 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- -1 n -butyl Chemical group 0.000 claims description 62
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 239000003814 drug Substances 0.000 claims description 34
- 208000035475 disorder Diseases 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229940124597 therapeutic agent Drugs 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 206010022489 Insulin Resistance Diseases 0.000 claims description 12
- 239000002671 adjuvant Substances 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 201000005948 Donohue syndrome Diseases 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000013066 combination product Substances 0.000 claims description 5
- 229940127555 combination product Drugs 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- IHRKWTFLZXFMCE-UHFFFAOYSA-N C(CCC)NCC(O)C=1C=CC(NC=1)=O Chemical compound C(CCC)NCC(O)C=1C=CC(NC=1)=O IHRKWTFLZXFMCE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000035369 Leprechaunism Diseases 0.000 claims description 4
- JKVXQXXHLXNCHC-VIFPVBQESA-N NC1=NC=CC(=N1)[C@H](CNCCCC)O Chemical compound NC1=NC=CC(=N1)[C@H](CNCCCC)O JKVXQXXHLXNCHC-VIFPVBQESA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- GAZJHWBIVVCJOZ-QRPNPIFTSA-N Cl.CCCCNC[C@H](O)c1csc(n1)C(F)(F)F Chemical compound Cl.CCCCNC[C@H](O)c1csc(n1)C(F)(F)F GAZJHWBIVVCJOZ-QRPNPIFTSA-N 0.000 claims description 3
- 208000031773 Insulin resistance syndrome Diseases 0.000 claims description 3
- 208000016140 Rabson-Mendenhall syndrome Diseases 0.000 claims description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 2
- IHINBCLAIJVIOH-UHFFFAOYSA-N C(CCC)NCC(O)C1=CC(NC=C1)=O Chemical compound C(CCC)NCC(O)C1=CC(NC=C1)=O IHINBCLAIJVIOH-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- COWGNGYZVVRZRK-QRPNPIFTSA-N Cl.CCCCNC[C@H](O)c1csc(N)n1 Chemical compound Cl.CCCCNC[C@H](O)c1csc(N)n1 COWGNGYZVVRZRK-QRPNPIFTSA-N 0.000 claims description 2
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 2
- 201000010272 acanthosis nigricans Diseases 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 claims description 2
- 239000000852 hydrogen donor Substances 0.000 claims description 2
- 201000010066 hyperandrogenism Diseases 0.000 claims description 2
- 208000006132 lipodystrophy Diseases 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 206010020718 hyperplasia Diseases 0.000 claims 1
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 230000000694 effects Effects 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- 238000004587 chromatography analysis Methods 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000011734 sodium Substances 0.000 description 29
- 102000004877 Insulin Human genes 0.000 description 27
- 108090001061 Insulin Proteins 0.000 description 27
- 229940125396 insulin Drugs 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- 239000012267 brine Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 230000004190 glucose uptake Effects 0.000 description 18
- 210000004369 blood Anatomy 0.000 description 17
- 239000008280 blood Substances 0.000 description 17
- 235000000346 sugar Nutrition 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- 208000010706 fatty liver disease Diseases 0.000 description 15
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 14
- 239000008103 glucose Substances 0.000 description 14
- 201000010099 disease Diseases 0.000 description 13
- 210000002027 skeletal muscle Anatomy 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 210000004185 liver Anatomy 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000002265 prevention Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 108091006300 SLC2A4 Proteins 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003925 fat Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 102100033939 Solute carrier family 2, facilitated glucose transporter member 4 Human genes 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 206010012601 diabetes mellitus Diseases 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- 230000001965 increasing effect Effects 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 108010001127 Insulin Receptor Proteins 0.000 description 8
- 208000008589 Obesity Diseases 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 235000020824 obesity Nutrition 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 231100000240 steatosis hepatitis Toxicity 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 206010016654 Fibrosis Diseases 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 230000007863 steatosis Effects 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 102000003746 Insulin Receptor Human genes 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000007882 cirrhosis Effects 0.000 description 6
- 208000019425 cirrhosis of liver Diseases 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000003834 intracellular effect Effects 0.000 description 6
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 6
- 238000007911 parenteral administration Methods 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000014101 glucose homeostasis Effects 0.000 description 5
- 208000006454 hepatitis Diseases 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- SCOJKGRNQDKFRP-UHFFFAOYSA-N 2-chloro-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CCl SCOJKGRNQDKFRP-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 4
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 102000042092 Glucose transporter family Human genes 0.000 description 4
- 108091052347 Glucose transporter family Proteins 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 210000000577 adipose tissue Anatomy 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000013475 authorization Methods 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 150000003943 catecholamines Chemical class 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 208000018191 liver inflammation Diseases 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 210000002363 skeletal muscle cell Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000005945 translocation Effects 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- GONVOEKOJWYKRU-UHFFFAOYSA-N 2-chloro-1-(5-fluoropyridin-3-yl)ethanone Chemical compound Fc1cncc(c1)C(=O)CCl GONVOEKOJWYKRU-UHFFFAOYSA-N 0.000 description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- IJAKLEKTAIWJTA-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C1=CC=C(C=N1)O Chemical compound C(C)(C)(C)NC[C@H](O)C1=CC=C(C=N1)O IJAKLEKTAIWJTA-JTQLQIEISA-N 0.000 description 3
- FEYHZZDRBBHTDF-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C1=NC=C(C=C1)F Chemical compound C(C)(C)(C)NC[C@H](O)C1=NC=C(C=C1)F FEYHZZDRBBHTDF-JTQLQIEISA-N 0.000 description 3
- KQQRVZQDFJTAEQ-UHFFFAOYSA-N C(CCC)NCC(O)C1=CC=NC=C1 Chemical compound C(CCC)NCC(O)C1=CC=NC=C1 KQQRVZQDFJTAEQ-UHFFFAOYSA-N 0.000 description 3
- ZCMQIUMCOIQXBS-JTQLQIEISA-N C(CCC)NC[C@H](O)C1=CN=C(S1)NC(C(C)C)=O Chemical compound C(CCC)NC[C@H](O)C1=CN=C(S1)NC(C(C)C)=O ZCMQIUMCOIQXBS-JTQLQIEISA-N 0.000 description 3
- XADJYUNCXJCQMC-YDALLXLXSA-N Cl.CCCCNC[C@H](O)c1cnc(NC(=O)C(C)C)nc1 Chemical compound Cl.CCCCNC[C@H](O)c1cnc(NC(=O)C(C)C)nc1 XADJYUNCXJCQMC-YDALLXLXSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 208000032928 Dyslipidaemia Diseases 0.000 description 3
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000007995 HEPES buffer Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 description 3
- 208000000501 Lipidoses Diseases 0.000 description 3
- 206010024585 Lipidosis Diseases 0.000 description 3
- NLNUKWATBOWBOE-UHFFFAOYSA-N N1=C(C(=O)CCl)C=CN=C1NC(=O)C(C)C Chemical compound N1=C(C(=O)CCl)C=CN=C1NC(=O)C(C)C NLNUKWATBOWBOE-UHFFFAOYSA-N 0.000 description 3
- 208000001280 Prediabetic State Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- 102000001708 Protein Isoforms Human genes 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 3
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 102000014384 Type C Phospholipases Human genes 0.000 description 3
- 108010079194 Type C Phospholipases Proteins 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000002648 combination therapy Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000003914 insulin secretion Effects 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000005229 liver cell Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 201000009104 prediabetes syndrome Diseases 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 3
- 230000011664 signaling Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- VMKAFJQFKBASMU-QGZVFWFLSA-N (r)-2-methyl-cbs-oxazaborolidine Chemical compound C([C@@H]12)CCN1B(C)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-QGZVFWFLSA-N 0.000 description 2
- VLELIZKJWKLDMD-UHFFFAOYSA-N 1-(2-amino-1,3-thiazol-4-yl)-2-bromoethanone Chemical compound NC1=NC(C(=O)CBr)=CS1 VLELIZKJWKLDMD-UHFFFAOYSA-N 0.000 description 2
- PEBHYBRSFPZAMD-UHFFFAOYSA-N 1-(3-phenylmethoxypyridin-4-yl)ethanone Chemical compound CC(=O)C1=CC=NC=C1OCC1=CC=CC=C1 PEBHYBRSFPZAMD-UHFFFAOYSA-N 0.000 description 2
- UMNJTLCRUSCDEW-UHFFFAOYSA-N 1-(5-phenylmethoxypyridin-2-yl)ethanone Chemical compound C1=NC(C(=O)C)=CC=C1OCC1=CC=CC=C1 UMNJTLCRUSCDEW-UHFFFAOYSA-N 0.000 description 2
- OVRSIQWVIJSERH-UHFFFAOYSA-N 1-(dimethylamino)-4,4-dimethoxypent-1-en-3-one Chemical compound COC(C)(OC)C(=O)C=CN(C)C OVRSIQWVIJSERH-UHFFFAOYSA-N 0.000 description 2
- VZBAIMIVLDKBTE-UHFFFAOYSA-N 2,2,2-trifluoroethanethioamide Chemical compound NC(=S)C(F)(F)F VZBAIMIVLDKBTE-UHFFFAOYSA-N 0.000 description 2
- ZBCWNFUTXYIEHE-UHFFFAOYSA-N 2-bromo-1-(3-chloropyridin-2-yl)ethanone;hydrobromide Chemical compound Br.ClC1=CC=CN=C1C(=O)CBr ZBCWNFUTXYIEHE-UHFFFAOYSA-N 0.000 description 2
- UAXQBCQWFKWRTA-UHFFFAOYSA-N 2-bromo-1-[2-(trifluoromethyl)-1,3-thiazol-4-yl]ethanone Chemical compound FC(F)(F)C1=NC(C(=O)CBr)=CS1 UAXQBCQWFKWRTA-UHFFFAOYSA-N 0.000 description 2
- VPTNAJLKKVQXRL-UHFFFAOYSA-N 2-bromo-1-pyridin-4-ylethanone;hydrochloride Chemical compound Cl.BrCC(=O)C1=CC=NC=C1 VPTNAJLKKVQXRL-UHFFFAOYSA-N 0.000 description 2
- LLEVUKSAMOQIJO-UHFFFAOYSA-N 2-chloro-1-(3-fluoropyridin-4-yl)ethanone Chemical compound FC1=CN=CC=C1C(=O)CCl LLEVUKSAMOQIJO-UHFFFAOYSA-N 0.000 description 2
- SCQMCNRCPKIWCD-UHFFFAOYSA-N 2-chloro-1-(5-chloropyridin-3-yl)ethanone Chemical compound ClCC(=O)c1cncc(Cl)c1 SCQMCNRCPKIWCD-UHFFFAOYSA-N 0.000 description 2
- CSKUFRDDRLPBPV-UHFFFAOYSA-N 2-chloro-1-(6-fluoropyridin-3-yl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C=N1 CSKUFRDDRLPBPV-UHFFFAOYSA-N 0.000 description 2
- UFQBSPGKRRSATO-UHFFFAOYSA-N 3,3-dimethoxybutan-2-one Chemical compound COC(C)(OC)C(C)=O UFQBSPGKRRSATO-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- YSHKYZAWTWKQKK-UHFFFAOYSA-N 3-bromo-5-phenylmethoxypyridine Chemical compound BrC1=CN=CC(OCC=2C=CC=CC=2)=C1 YSHKYZAWTWKQKK-UHFFFAOYSA-N 0.000 description 2
- GNHWZRZIPQSPAM-UHFFFAOYSA-N 4-(1,1-dimethoxyethyl)pyrimidin-2-amine Chemical compound COC(C)(OC)C1=CC=NC(N)=N1 GNHWZRZIPQSPAM-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- YFOQSLIPUHGGQE-UHFFFAOYSA-N 4-bromo-1-methylpyridin-2-one Chemical compound CN1C=CC(Br)=CC1=O YFOQSLIPUHGGQE-UHFFFAOYSA-N 0.000 description 2
- BBTGUOBUBJNAGS-UHFFFAOYSA-N 6-phenylmethoxypyridine-3-carbaldehyde Chemical compound N1=CC(C=O)=CC=C1OCC1=CC=CC=C1 BBTGUOBUBJNAGS-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 108010011376 AMP-Activated Protein Kinases Proteins 0.000 description 2
- 102000014156 AMP-Activated Protein Kinases Human genes 0.000 description 2
- 206010000599 Acromegaly Diseases 0.000 description 2
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FWHJNKVQMMWVMS-UHFFFAOYSA-N BrCC(=O)C=1N=C(SC=1)NC(C(C)C)=O Chemical compound BrCC(=O)C=1N=C(SC=1)NC(C(C)C)=O FWHJNKVQMMWVMS-UHFFFAOYSA-N 0.000 description 2
- DVAULACNHUHBAM-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C1=C(C=NC=C1)F Chemical compound C(C)(C)(C)NC[C@H](O)C1=C(C=NC=C1)F DVAULACNHUHBAM-JTQLQIEISA-N 0.000 description 2
- ZUHATPRIWKNORQ-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C=1C=NC=C(C=1)Cl Chemical compound C(C)(C)(C)NC[C@H](O)C=1C=NC=C(C=1)Cl ZUHATPRIWKNORQ-JTQLQIEISA-N 0.000 description 2
- SASMSPQPEDQJII-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C=1C=NC=C(C=1)F Chemical compound C(C)(C)(C)NC[C@H](O)C=1C=NC=C(C=1)F SASMSPQPEDQJII-JTQLQIEISA-N 0.000 description 2
- MBOSHWYIAMTZBC-UHFFFAOYSA-N C(C1=CC=CC=C1)N(CC(O)C=1C=NC(=CC=1)OCC1=CC=CC=C1)CCCC Chemical compound C(C1=CC=CC=C1)N(CC(O)C=1C=NC(=CC=1)OCC1=CC=CC=C1)CCCC MBOSHWYIAMTZBC-UHFFFAOYSA-N 0.000 description 2
- OBUDCWWVFBLWJU-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=NC=C(C=C1)C1OC1 Chemical compound C(C1=CC=CC=C1)OC1=NC=C(C=C1)C1OC1 OBUDCWWVFBLWJU-UHFFFAOYSA-N 0.000 description 2
- LXGRQQHKWSXMHM-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C(C=NC=1)C(CCl)=O Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=NC=1)C(CCl)=O LXGRQQHKWSXMHM-UHFFFAOYSA-N 0.000 description 2
- FNZTUMMTNHGGHT-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=CC(=NC=1)C(CBr)=O Chemical compound C(C1=CC=CC=C1)OC=1C=CC(=NC=1)C(CBr)=O FNZTUMMTNHGGHT-UHFFFAOYSA-N 0.000 description 2
- WOTQNVDVSPZLGN-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=CC(=NC=1)C(CCl)=O Chemical compound C(C1=CC=CC=C1)OC=1C=CC(=NC=1)C(CCl)=O WOTQNVDVSPZLGN-UHFFFAOYSA-N 0.000 description 2
- ZVJVOAKDRAOECT-KRWDZBQOSA-N C(C1=CC=CC=C1)OC=1C=CC(=NC=1)[C@H](CNC(C)(C)C)O Chemical compound C(C1=CC=CC=C1)OC=1C=CC(=NC=1)[C@H](CNC(C)(C)C)O ZVJVOAKDRAOECT-KRWDZBQOSA-N 0.000 description 2
- UKSHDABBIUQWQN-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=NC=CC=1C(CBr)=O Chemical compound C(C1=CC=CC=C1)OC=1C=NC=CC=1C(CBr)=O UKSHDABBIUQWQN-UHFFFAOYSA-N 0.000 description 2
- HAKBSFCATUJDRZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=NC=CC=1C(CNC(C)(C)C)O Chemical compound C(C1=CC=CC=C1)OC=1C=NC=CC=1C(CNC(C)(C)C)O HAKBSFCATUJDRZ-UHFFFAOYSA-N 0.000 description 2
- IQPSKFDYEFBPMF-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=NC=CC=1C1OC1 Chemical compound C(C1=CC=CC=C1)OC=1C=NC=CC=1C1OC1 IQPSKFDYEFBPMF-UHFFFAOYSA-N 0.000 description 2
- XVWQJFNEOWOZOQ-UHFFFAOYSA-N C(CCC)NCC(O)C=1C=NC=CC=1 Chemical compound C(CCC)NCC(O)C=1C=NC=CC=1 XVWQJFNEOWOZOQ-UHFFFAOYSA-N 0.000 description 2
- WGPGHLSVWWNYFW-ZETCQYMHSA-N C1(=C([C@@H](O)CCl)C=CN=C1)F Chemical compound C1(=C([C@@H](O)CCl)C=CN=C1)F WGPGHLSVWWNYFW-ZETCQYMHSA-N 0.000 description 2
- FQSWSZHTDJQVMG-QMMMGPOBSA-N C1(=CC=NC(NC(=O)C(C)C)=N1)[C@H]1OC1 Chemical compound C1(=CC=NC(NC(=O)C(C)C)=N1)[C@H]1OC1 FQSWSZHTDJQVMG-QMMMGPOBSA-N 0.000 description 2
- PMXRJFSMOIPNNU-ZETCQYMHSA-N C1(=CN=CC([C@@H](O)CCl)=C1)Cl Chemical compound C1(=CN=CC([C@@H](O)CCl)=C1)Cl PMXRJFSMOIPNNU-ZETCQYMHSA-N 0.000 description 2
- RLMLQGNWPAOECZ-UHFFFAOYSA-N C1=C(C(=O)CCl)C=CN(C1=O)C Chemical compound C1=C(C(=O)CCl)C=CN(C1=O)C RLMLQGNWPAOECZ-UHFFFAOYSA-N 0.000 description 2
- DSIXLHKRHFFXJP-UHFFFAOYSA-N C1=CC(=NC(=N1)NC(=O)C(C)C)C(OC)(OC)C Chemical compound C1=CC(=NC(=N1)NC(=O)C(C)C)C(OC)(OC)C DSIXLHKRHFFXJP-UHFFFAOYSA-N 0.000 description 2
- ZKWXVWXMOIKFGG-LURJTMIESA-N C1=CC=NC(=C1Cl)[C@@H](O)CCl Chemical compound C1=CC=NC(=C1Cl)[C@@H](O)CCl ZKWXVWXMOIKFGG-LURJTMIESA-N 0.000 description 2
- ASSSMQLKODVFDC-UHFFFAOYSA-N CC(C)C(=O)NC1=NC=C(S1)C(O)=O Chemical compound CC(C)C(=O)NC1=NC=C(S1)C(O)=O ASSSMQLKODVFDC-UHFFFAOYSA-N 0.000 description 2
- HUNUHEIRRISDLA-UHFFFAOYSA-N Cl.CC(C)(C)NCC(O)c1ccncc1O Chemical compound Cl.CC(C)(C)NCC(O)c1ccncc1O HUNUHEIRRISDLA-UHFFFAOYSA-N 0.000 description 2
- AGXXPBPJTFMDKR-XRIOVQLTSA-N Cl.Cl.CC(C)(C)NC[C@H](O)c1ccc(Cl)cn1 Chemical compound Cl.Cl.CC(C)(C)NC[C@H](O)c1ccc(Cl)cn1 AGXXPBPJTFMDKR-XRIOVQLTSA-N 0.000 description 2
- JNQFKJVFZQWFDP-XRIOVQLTSA-N Cl.Cl.CC(C)(C)NC[C@H](O)c1cncc(O)c1 Chemical compound Cl.Cl.CC(C)(C)NC[C@H](O)c1cncc(O)c1 JNQFKJVFZQWFDP-XRIOVQLTSA-N 0.000 description 2
- MSHQDRQYHDAHDQ-WWPIYYJJSA-N Cl.Cl.CC(C)(C)NC[C@H](O)c1ncccc1Cl Chemical compound Cl.Cl.CC(C)(C)NC[C@H](O)c1ncccc1Cl MSHQDRQYHDAHDQ-WWPIYYJJSA-N 0.000 description 2
- GNEMLHZECHCGDM-KLXURFKVSA-N Cl.Cl.CCCCNC[C@H](O)c1cnc(N)s1 Chemical compound Cl.Cl.CCCCNC[C@H](O)c1cnc(N)s1 GNEMLHZECHCGDM-KLXURFKVSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 229920002527 Glycogen Polymers 0.000 description 2
- 206010019663 Hepatic failure Diseases 0.000 description 2
- 206010019708 Hepatic steatosis Diseases 0.000 description 2
- 229940122355 Insulin sensitizer Drugs 0.000 description 2
- 208000017034 Insulin-resistance syndrome type A Diseases 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 208000002720 Malnutrition Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- ADYCUVNWNAHQOQ-UHFFFAOYSA-N N1=C(C(=C)OC)C=CN=C1NC(=O)C(C)C Chemical compound N1=C(C(=C)OC)C=CN=C1NC(=O)C(C)C ADYCUVNWNAHQOQ-UHFFFAOYSA-N 0.000 description 2
- LGWOTPCFWSHJMG-QMMMGPOBSA-N NC=1SC=C(N=1)[C@H](CNCCCC)O Chemical compound NC=1SC=C(N=1)[C@H](CNCCCC)O LGWOTPCFWSHJMG-QMMMGPOBSA-N 0.000 description 2
- VEWMLSSPWCVTLG-AWEZNQCLSA-N O(C1=CN=C([C@H]2OC2)C=C1)CC1=CC=CC=C1 Chemical compound O(C1=CN=C([C@H]2OC2)C=C1)CC1=CC=CC=C1 VEWMLSSPWCVTLG-AWEZNQCLSA-N 0.000 description 2
- 108091007960 PI3Ks Proteins 0.000 description 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 108091006296 SLC2A1 Proteins 0.000 description 2
- 102100023536 Solute carrier family 2, facilitated glucose transporter member 1 Human genes 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 102100040257 TBC1 domain family member 4 Human genes 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 235000013681 dietary sucrose Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229950009769 etabonate Drugs 0.000 description 2
- 238000009207 exercise therapy Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000009229 glucose formation Effects 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- 229940096919 glycogen Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 208000001921 latent autoimmune diabetes in adults Diseases 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 231100000835 liver failure Toxicity 0.000 description 2
- 208000007903 liver failure Diseases 0.000 description 2
- CHHXEZSCHQVSRE-UHFFFAOYSA-N lobeglitazone Chemical compound C1=CC(OC)=CC=C1OC1=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=NC=N1 CHHXEZSCHQVSRE-UHFFFAOYSA-N 0.000 description 2
- 229950007685 lobeglitazone Drugs 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001071 malnutrition Effects 0.000 description 2
- 235000000824 malnutrition Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- 229960003105 metformin Drugs 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 210000000663 muscle cell Anatomy 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 210000003098 myoblast Anatomy 0.000 description 2
- UUWLAHVKCXPZSI-UHFFFAOYSA-N n-(5-bromopyrimidin-2-yl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=NC=C(Br)C=N1 UUWLAHVKCXPZSI-UHFFFAOYSA-N 0.000 description 2
- NGGXACLSAZXJGM-UHFFFAOYSA-N n-(diaminomethylidene)acetamide Chemical compound CC(=O)N=C(N)N NGGXACLSAZXJGM-UHFFFAOYSA-N 0.000 description 2
- LJUFCBXTAWRSSE-UHFFFAOYSA-N n-[5-(2-bromoacetyl)pyrimidin-2-yl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=NC=C(C(=O)CBr)C=N1 LJUFCBXTAWRSSE-UHFFFAOYSA-N 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 208000015380 nutritional deficiency disease Diseases 0.000 description 2
- 229940126701 oral medication Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 2
- 229960001641 troglitazone Drugs 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- XFUFEUMGWJCPMR-ZETCQYMHSA-N (1r)-2-chloro-1-(5-fluoropyridin-2-yl)ethanol Chemical compound ClC[C@H](O)C1=CC=C(F)C=N1 XFUFEUMGWJCPMR-ZETCQYMHSA-N 0.000 description 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GMXZSVFWDQBSFR-UHFFFAOYSA-N 1-(3-chloropyridin-2-yl)ethanone Chemical compound CC(=O)C1=NC=CC=C1Cl GMXZSVFWDQBSFR-UHFFFAOYSA-N 0.000 description 1
- REYSBWKWFPSDDR-UHFFFAOYSA-N 1-(3-hydroxypyridin-4-yl)ethanone Chemical compound CC(=O)C1=CC=NC=C1O REYSBWKWFPSDDR-UHFFFAOYSA-N 0.000 description 1
- VVYMEQBXUFPILB-UHFFFAOYSA-N 1-(5-chloropyridin-2-yl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=N1 VVYMEQBXUFPILB-UHFFFAOYSA-N 0.000 description 1
- WESGRMTVUPBJHT-UHFFFAOYSA-N 1-(5-hydroxypyridin-2-yl)ethanone Chemical compound CC(=O)C1=CC=C(O)C=N1 WESGRMTVUPBJHT-UHFFFAOYSA-N 0.000 description 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- DVAULACNHUHBAM-UHFFFAOYSA-N 2-(tert-butylamino)-1-(3-fluoropyridin-4-yl)ethanol Chemical compound CC(C)(C)NCC(O)c1ccncc1F DVAULACNHUHBAM-UHFFFAOYSA-N 0.000 description 1
- SASMSPQPEDQJII-UHFFFAOYSA-N 2-(tert-butylamino)-1-(5-fluoropyridin-3-yl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CN=CC(F)=C1 SASMSPQPEDQJII-UHFFFAOYSA-N 0.000 description 1
- ZFMRDDYYJJCBKC-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-carboxylic acid Chemical compound NC1=NC=C(C(O)=O)S1 ZFMRDDYYJJCBKC-UHFFFAOYSA-N 0.000 description 1
- UODINHBLNPPDPD-UHFFFAOYSA-N 2-bromo-5-fluoropyridine Chemical compound FC1=CC=C(Br)N=C1 UODINHBLNPPDPD-UHFFFAOYSA-N 0.000 description 1
- JUSXLWAFYVKNLT-UHFFFAOYSA-M 2-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1Br JUSXLWAFYVKNLT-UHFFFAOYSA-M 0.000 description 1
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical compound CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 description 1
- GITHJELHBRVEGE-UHFFFAOYSA-N 2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound CC(C)C(=O)NC1=NC=CS1 GITHJELHBRVEGE-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- IDDXMCNSHNXTRS-UHFFFAOYSA-N 2-oxo-1h-pyridine-4-carbaldehyde Chemical compound OC1=CC(C=O)=CC=N1 IDDXMCNSHNXTRS-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 1
- BELDOPUBSLPBCQ-UHFFFAOYSA-N 3-bromo-5-chloropyridine Chemical compound ClC1=CN=CC(Br)=C1 BELDOPUBSLPBCQ-UHFFFAOYSA-N 0.000 description 1
- HNNNBQRRIHKFLI-UHFFFAOYSA-N 3-bromo-5-fluoropyridine Chemical compound FC1=CN=CC(Br)=C1 HNNNBQRRIHKFLI-UHFFFAOYSA-N 0.000 description 1
- CELKOWQJPVJKIL-UHFFFAOYSA-N 3-fluoropyridine Chemical compound FC1=CC=CN=C1 CELKOWQJPVJKIL-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- SSLMGOKTIUIZLY-UHFFFAOYSA-N 4-bromo-1h-pyridin-2-one Chemical compound OC1=CC(Br)=CC=N1 SSLMGOKTIUIZLY-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UHRHPPKWXSNZLR-UHFFFAOYSA-N 5-bromopyrimidin-2-amine Chemical compound NC1=NC=C(Br)C=N1 UHRHPPKWXSNZLR-UHFFFAOYSA-N 0.000 description 1
- VQDBNKDJNJQRDG-NSHDSACASA-N 6-[(1s)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-NSHDSACASA-N 0.000 description 1
- IJAKLEKTAIWJTA-UHFFFAOYSA-N 6-[2-(tert-butylamino)-1-hydroxyethyl]pyridin-3-ol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C=N1 IJAKLEKTAIWJTA-UHFFFAOYSA-N 0.000 description 1
- BUMAFTGGYPBHHK-UHFFFAOYSA-N 6-oxo-1h-pyridine-3-carbaldehyde Chemical compound O=CC=1C=CC(=O)NC=1 BUMAFTGGYPBHHK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 101100297694 Arabidopsis thaliana PIP2-7 gene Proteins 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LDKQSHJUMMKDDX-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C1=C(C=NC=C1)O Chemical compound C(C)(C)(C)NCC(O)C1=C(C=NC=C1)O LDKQSHJUMMKDDX-UHFFFAOYSA-N 0.000 description 1
- HAZSXBGMLLEIRH-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C1=CC(N(C=C1)C)=O Chemical compound C(C)(C)(C)NCC(O)C1=CC(N(C=C1)C)=O HAZSXBGMLLEIRH-UHFFFAOYSA-N 0.000 description 1
- GRYWBABTDBOWLW-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C1=NC=C(C=C1)Cl Chemical compound C(C)(C)(C)NCC(O)C1=NC=C(C=C1)Cl GRYWBABTDBOWLW-UHFFFAOYSA-N 0.000 description 1
- FEYHZZDRBBHTDF-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C1=NC=C(C=C1)F Chemical compound C(C)(C)(C)NCC(O)C1=NC=C(C=C1)F FEYHZZDRBBHTDF-UHFFFAOYSA-N 0.000 description 1
- NOKBSXAUOZHETJ-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C1=NC=CC=C1Cl Chemical compound C(C)(C)(C)NCC(O)C1=NC=CC=C1Cl NOKBSXAUOZHETJ-UHFFFAOYSA-N 0.000 description 1
- YILBDXSOBOEIOC-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C=1C=C(C=NC=1)O Chemical compound C(C)(C)(C)NCC(O)C=1C=C(C=NC=1)O YILBDXSOBOEIOC-UHFFFAOYSA-N 0.000 description 1
- ZUHATPRIWKNORQ-UHFFFAOYSA-N C(C)(C)(C)NCC(O)C=1C=NC=C(C=1)Cl Chemical compound C(C)(C)(C)NCC(O)C=1C=NC=C(C=1)Cl ZUHATPRIWKNORQ-UHFFFAOYSA-N 0.000 description 1
- GRYWBABTDBOWLW-JTQLQIEISA-N C(C)(C)(C)NC[C@H](O)C1=NC=C(C=C1)Cl Chemical compound C(C)(C)(C)NC[C@H](O)C1=NC=C(C=C1)Cl GRYWBABTDBOWLW-JTQLQIEISA-N 0.000 description 1
- NOKBSXAUOZHETJ-VIFPVBQESA-N C(C)(C)(C)NC[C@H](O)C1=NC=CC=C1Cl Chemical compound C(C)(C)(C)NC[C@H](O)C1=NC=CC=C1Cl NOKBSXAUOZHETJ-VIFPVBQESA-N 0.000 description 1
- AJWPBIGMZDVIPB-UHFFFAOYSA-N C(C)OC(=C)C=1C=NC(=NC=1)NC(C(C)C)=O Chemical compound C(C)OC(=C)C=1C=NC(=NC=1)NC(C(C)C)=O AJWPBIGMZDVIPB-UHFFFAOYSA-N 0.000 description 1
- ZCMQIUMCOIQXBS-UHFFFAOYSA-N C(CCC)NCC(O)C1=CN=C(S1)NC(C(C)C)=O Chemical compound C(CCC)NCC(O)C1=CN=C(S1)NC(C(C)C)=O ZCMQIUMCOIQXBS-UHFFFAOYSA-N 0.000 description 1
- XAXKXBSMQVAOGB-UHFFFAOYSA-N C(CCC)NCC(O)C=1C=NC(=NC=1)NC(C(C)C)=O Chemical compound C(CCC)NCC(O)C=1C=NC(=NC=1)NC(C(C)C)=O XAXKXBSMQVAOGB-UHFFFAOYSA-N 0.000 description 1
- HISFECHZTYALFJ-UHFFFAOYSA-N C(CCC)NCC(O)C=1N=C(SC=1)C(F)(F)F Chemical compound C(CCC)NCC(O)C=1N=C(SC=1)C(F)(F)F HISFECHZTYALFJ-UHFFFAOYSA-N 0.000 description 1
- HISFECHZTYALFJ-QMMMGPOBSA-N C(CCC)NC[C@H](O)C=1N=C(SC=1)C(F)(F)F Chemical compound C(CCC)NC[C@H](O)C=1N=C(SC=1)C(F)(F)F HISFECHZTYALFJ-QMMMGPOBSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- HAZSXBGMLLEIRH-JTQLQIEISA-N C1(=O)C=C([C@@H](O)CNC(C)(C)C)C=CN1C Chemical compound C1(=O)C=C([C@@H](O)CNC(C)(C)C)C=CN1C HAZSXBGMLLEIRH-JTQLQIEISA-N 0.000 description 1
- VCLCUGAHNUSJRP-ZETCQYMHSA-N C1(Cl)=CC=C([C@@H](O)CCl)N=C1 Chemical compound C1(Cl)=CC=C([C@@H](O)CCl)N=C1 VCLCUGAHNUSJRP-ZETCQYMHSA-N 0.000 description 1
- FMUVIUMVWBPFCS-AWEZNQCLSA-N C1(OCC2=CC=CC=C2)=CN=C(C=C1)[C@@H](O)CCl Chemical compound C1(OCC2=CC=CC=C2)=CN=C(C=C1)[C@@H](O)CCl FMUVIUMVWBPFCS-AWEZNQCLSA-N 0.000 description 1
- ZTNVCELZYMUFKX-UHFFFAOYSA-N C=1(SC(=NC=1)NC(=O)C(C)C)C(=O)CBr Chemical compound C=1(SC(=NC=1)NC(=O)C(C)C)C(=O)CBr ZTNVCELZYMUFKX-UHFFFAOYSA-N 0.000 description 1
- AENDZUWMEKBNNJ-UHFFFAOYSA-N CC(O)=O.CCCCNCC(O)c1cc[nH]c(=O)c1 Chemical compound CC(O)=O.CCCCNCC(O)c1cc[nH]c(=O)c1 AENDZUWMEKBNNJ-UHFFFAOYSA-N 0.000 description 1
- QVLTVILSYOWFRM-UHFFFAOYSA-L CC1=C(C)C(C)([Rh](Cl)Cl)C(C)=C1C Chemical class CC1=C(C)C(C)([Rh](Cl)Cl)C(C)=C1C QVLTVILSYOWFRM-UHFFFAOYSA-L 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GNEMLHZECHCGDM-UHFFFAOYSA-N Cl.Cl.CCCCNCC(O)c1cnc(N)s1 Chemical compound Cl.Cl.CCCCNCC(O)c1cnc(N)s1 GNEMLHZECHCGDM-UHFFFAOYSA-N 0.000 description 1
- HCVXZRLTCBIBJG-UHFFFAOYSA-N ClCC(=O)C1=NC=CC=C1Cl Chemical compound ClCC(=O)C1=NC=CC=C1Cl HCVXZRLTCBIBJG-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010068271 Cystic fibrosis related diabetes Diseases 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- SDKQRNRRDYRQKY-UHFFFAOYSA-N Dioxacarb Chemical compound CNC(=O)OC1=CC=CC=C1C1OCCO1 SDKQRNRRDYRQKY-UHFFFAOYSA-N 0.000 description 1
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 description 1
- 206010013554 Diverticulum Diseases 0.000 description 1
- DVJAMEIQRSHVKC-BDAKNGLRSA-N Dutogliptin Chemical compound OB(O)[C@@H]1CCCN1C(=O)CN[C@H]1CNCC1 DVJAMEIQRSHVKC-BDAKNGLRSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- ZWPRRQZNBDYKLH-VIFPVBQESA-N Gemigliptin Chemical compound C([C@@H](N)CC(=O)N1CC2=C(C(=NC(=N2)C(F)(F)F)C(F)(F)F)CC1)N1CC(F)(F)CCC1=O ZWPRRQZNBDYKLH-VIFPVBQESA-N 0.000 description 1
- HNSCCNJWTJUGNQ-UHFFFAOYSA-N Glyclopyramide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)NN1CCCC1 HNSCCNJWTJUGNQ-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
- 206010019837 Hepatocellular injury Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000891625 Homo sapiens TBC1 domain family member 4 Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108010002386 Interleukin-3 Proteins 0.000 description 1
- 206010023379 Ketoacidosis Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- IXJSBOKTCWFOAM-QMMMGPOBSA-N N1=C([C@@H](O)CCl)C=CN=C1NC(=O)C(C)C Chemical compound N1=C([C@@H](O)CCl)C=CN=C1NC(=O)C(C)C IXJSBOKTCWFOAM-QMMMGPOBSA-N 0.000 description 1
- ZBGWJEIINMTCOA-UHFFFAOYSA-N NC1=NC=C(C=N1)C(CNCCCC)O Chemical compound NC1=NC=C(C=N1)C(CNCCCC)O ZBGWJEIINMTCOA-UHFFFAOYSA-N 0.000 description 1
- ZBGWJEIINMTCOA-VIFPVBQESA-N NC1=NC=C(C=N1)[C@H](CNCCCC)O Chemical compound NC1=NC=C(C=N1)[C@H](CNCCCC)O ZBGWJEIINMTCOA-VIFPVBQESA-N 0.000 description 1
- JKVXQXXHLXNCHC-UHFFFAOYSA-N NC1=NC=CC(=N1)C(CNCCCC)O Chemical compound NC1=NC=CC(=N1)C(CNCCCC)O JKVXQXXHLXNCHC-UHFFFAOYSA-N 0.000 description 1
- LGWOTPCFWSHJMG-UHFFFAOYSA-N NC=1SC=C(N=1)C(CNCCCC)O Chemical compound NC=1SC=C(N=1)C(CNCCCC)O LGWOTPCFWSHJMG-UHFFFAOYSA-N 0.000 description 1
- 229910017855 NH 4 F Inorganic materials 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 208000007944 Nodular Nonsuppurative Panniculitis Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GSINGUMRKGRYJP-VZWAGXQNSA-N Remogliflozin Chemical compound C1=CC(OC(C)C)=CC=C1CC1=C(C)N(C(C)C)N=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 GSINGUMRKGRYJP-VZWAGXQNSA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 1
- 108091006299 SLC2A2 Proteins 0.000 description 1
- 108091006298 SLC2A3 Proteins 0.000 description 1
- 101100456541 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MEC3 gene Proteins 0.000 description 1
- 101100483663 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UFD1 gene Proteins 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 1
- 102100023537 Solute carrier family 2, facilitated glucose transporter member 2 Human genes 0.000 description 1
- 102100022722 Solute carrier family 2, facilitated glucose transporter member 3 Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 101710107476 TBC1 domain family member 4 Proteins 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000026736 Weber-Christian disease Diseases 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
- 229960001466 acetohexamide Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 208000002353 alcoholic hepatitis Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 238000003016 alphascreen Methods 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940000806 amaryl Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003263 anabolic agent Substances 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 229950009977 anagliptin Drugs 0.000 description 1
- LDXYBEHACFJIEL-HNNXBMFYSA-N anagliptin Chemical compound C=1N2N=C(C)C=C2N=CC=1C(=O)NCC(C)(C)NCC(=O)N1CCC[C@H]1C#N LDXYBEHACFJIEL-HNNXBMFYSA-N 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RDUHXGIIUDVSHR-UHFFFAOYSA-N bamethan Chemical compound CCCCNCC(O)C1=CC=C(O)C=C1 RDUHXGIIUDVSHR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 230000003491 cAMP production Effects 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229960001713 canagliflozin Drugs 0.000 description 1
- VHOFTEAWFCUTOS-TUGBYPPCSA-N canagliflozin hydrate Chemical compound O.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1 VHOFTEAWFCUTOS-TUGBYPPCSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 229960003362 carbutamide Drugs 0.000 description 1
- 230000003683 cardiac damage Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000005800 cardiovascular problem Effects 0.000 description 1
- 230000001925 catabolic effect Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 210000004262 dental pulp cavity Anatomy 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 229950003693 dutogliptin Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229960002458 gemigliptin Drugs 0.000 description 1
- 230000009395 genetic defect Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 208000004104 gestational diabetes Diseases 0.000 description 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical group O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 238000007446 glucose tolerance test Methods 0.000 description 1
- 230000006377 glucose transport Effects 0.000 description 1
- 229940088991 glucotrol Drugs 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 229950002888 glyclopyramide Drugs 0.000 description 1
- 208000007345 glycogen storage disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 230000037219 healthy weight Effects 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000004155 insulin signaling pathway Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229950000991 ipragliflozin Drugs 0.000 description 1
- AHFWIQIYAXSLBA-RQXATKFSSA-N ipragliflozin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(F)C(CC=2SC3=CC=CC=C3C=2)=C1 AHFWIQIYAXSLBA-RQXATKFSSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229960002397 linagliptin Drugs 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 231100000849 liver cell damage Toxicity 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000031852 maintenance of location in cell Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
- UOPFIWYXBIHPIP-SFTDATJTSA-N n-[(1s,2s)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 UOPFIWYXBIHPIP-SFTDATJTSA-N 0.000 description 1
- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229950000074 omarigliptin Drugs 0.000 description 1
- MKMPWKUAHLTIBJ-ISTRZQFTSA-N omarigliptin Chemical compound C1([C@H]2OC[C@@H](C[C@@H]2N)N2CC3=CN(N=C3C2)S(=O)(=O)C)=CC(F)=CC=C1F MKMPWKUAHLTIBJ-ISTRZQFTSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- GCYXWQUSHADNBF-AAEALURTSA-N preproglucagon 78-108 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 GCYXWQUSHADNBF-AAEALURTSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229940126844 remogliflozin Drugs 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960004937 saxagliptin Drugs 0.000 description 1
- QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 description 1
- 108010033693 saxagliptin Proteins 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229960004034 sitagliptin Drugs 0.000 description 1
- MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- JJXOIFHXNBFRNV-UHFFFAOYSA-N tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C JJXOIFHXNBFRNV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000030968 tissue homeostasis Effects 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000021476 total parenteral nutrition Nutrition 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 230000003820 β-cell dysfunction Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020237043200A KR20230175328A (ko) | 2017-09-13 | 2018-09-13 | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB1714745.5A GB201714745D0 (en) | 2017-09-13 | 2017-09-13 | New compounds and uses |
GB1714745.5 | 2017-09-13 | ||
PCT/GB2018/052595 WO2019053427A1 (en) | 2017-09-13 | 2018-09-13 | HETEROARYL SUBSTITUTED BETA-HYDROXYETHYLAMINO FOR USE IN THE TREATMENT OF HYPERGLYCEMIA |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020237043200A Division KR20230175328A (ko) | 2017-09-13 | 2018-09-13 | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20200052936A true KR20200052936A (ko) | 2020-05-15 |
Family
ID=60117187
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020207010465A KR20200052936A (ko) | 2017-09-13 | 2018-09-13 | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 |
KR1020237043200A KR20230175328A (ko) | 2017-09-13 | 2018-09-13 | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020237043200A KR20230175328A (ko) | 2017-09-13 | 2018-09-13 | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 |
Country Status (22)
Country | Link |
---|---|
US (2) | US11357757B2 (pl) |
EP (2) | EP3971168A1 (pl) |
JP (2) | JP7358338B2 (pl) |
KR (2) | KR20200052936A (pl) |
CN (1) | CN111315726A (pl) |
AU (1) | AU2018332501B2 (pl) |
BR (1) | BR112020005113A2 (pl) |
CA (1) | CA3075707A1 (pl) |
CY (1) | CY1125004T1 (pl) |
ES (1) | ES2902073T3 (pl) |
GB (1) | GB201714745D0 (pl) |
HR (1) | HRP20220177T1 (pl) |
HU (1) | HUE057426T2 (pl) |
IL (1) | IL273180A (pl) |
LT (1) | LT3681872T (pl) |
MX (2) | MX2020002825A (pl) |
PL (1) | PL3681872T3 (pl) |
PT (1) | PT3681872T (pl) |
RS (1) | RS62895B1 (pl) |
RU (1) | RU2020108523A (pl) |
SI (1) | SI3681872T1 (pl) |
WO (1) | WO2019053427A1 (pl) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
JP2022527769A (ja) | 2019-03-27 | 2022-06-06 | キュラセン セラピューティクス インコーポレイテッド | ベータアドレナリンアゴニスト及びそれを使用する方法 |
CA3144093A1 (en) * | 2019-07-01 | 2021-01-07 | Curasen Therapeutics, Inc. | Beta adrenergic agonist and methods of using the same |
JP2023528450A (ja) * | 2020-06-04 | 2023-07-04 | キュラセン セラピューティクス インコーポレイテッド | ベータアドレナリンアゴニストの形態及び組成物 |
GB202015035D0 (en) * | 2020-09-23 | 2020-11-04 | Atrogi Ab | New compounds and methods |
GB202015044D0 (en) * | 2020-09-23 | 2020-11-04 | Atrogi Ab | New compounds and methods |
GB2613616A (en) | 2021-12-09 | 2023-06-14 | Atrogi Ab | New formulations |
WO2024153813A1 (en) | 2023-01-20 | 2024-07-25 | Atrogi Ab | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
GB202304652D0 (en) * | 2023-03-29 | 2023-05-10 | Atrogi Ab | New compounds and medical uses thereof |
Family Cites Families (164)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE45721C (pl) | ||||
DE638650C (de) | 1934-06-08 | 1936-11-20 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von 3, 4-Dioxyphenylmonoalkylaminobutanolen-1 |
US2308232A (en) | 1939-01-17 | 1943-01-12 | Scheuing Georg | Isopropylaminomethyl-(3, 4-dioxyphenyl) carbinol |
US2460144A (en) | 1946-04-11 | 1949-01-25 | Sterling Drug Inc | Hydroxyphenyl alkanolamines |
FR1165845A (fr) | 1955-05-28 | 1958-10-29 | Philips Nv | Amines secondaires portant des substituants et leur préparation |
FR1324914A (fr) | 1961-01-11 | 1963-04-26 | Philips Nv | Procédé de préparation d'aralkylamines substituées optiquement actives |
DE1275069B (de) | 1960-02-15 | 1968-08-14 | Boehringer Sohn Ingelheim | 1-(3', 5'-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoalkane und Verfahren zu ihrer Herstellung |
NL6401871A (pl) | 1964-02-27 | 1965-08-30 | ||
GB1142508A (en) * | 1966-04-27 | 1969-02-12 | Whitefin Holding Sa | Pyrrole derivatives |
SE335359B (pl) | 1966-10-19 | 1971-05-24 | Draco Ab | |
AT285583B (de) | 1968-10-10 | 1970-11-10 | Chemie Linz Ag | Verfahren zur Herstellung von N,N'-bis-[2-(3',4'-Dihydroxyphenyl)-2-hydroxyäthyl]-hexamethylendiamin und seinen Salzen |
NO129903B (pl) | 1969-04-01 | 1974-06-10 | Sterling Drug Inc | |
GB1321701A (en) | 1969-10-01 | 1973-06-27 | Continental Pharma | Amino-alcohols their salts and process for prepairing the same |
US3910934A (en) | 1970-05-21 | 1975-10-07 | Minnesota Mining & Mfg | Process for the preparation of {60 -(hydroxy and alkoxy substituted)phenyl-{60 -(2-piperidinyl)-methanols |
GB1298494A (en) | 1970-06-17 | 1972-12-06 | Allen & Hanburys Ltd | Phenylethanolamine derivatives |
DE2157040A1 (de) | 1971-11-17 | 1973-05-24 | Thomae Gmbh Dr K | Neues verfahren zur herstellung von 4-amino-3,5-dihalogen-phenyl-aethanolaminen |
US3801631A (en) | 1972-02-16 | 1974-04-02 | Mead Johnson & Co | 2'-hydroxy-5'-(1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl)meth-anesulfonanilide and its salts |
DE2300614A1 (de) | 1973-01-08 | 1974-07-18 | Thomae Gmbh Dr K | Neue optisch aktive verbindungen |
DE2259282A1 (de) | 1972-12-04 | 1974-06-12 | Thomae Gmbh Dr K | Neue aminoaethanole |
US4119710A (en) | 1972-12-18 | 1978-10-10 | Boehringer Ingelheim Gmbh | Bronchospasmolytic 1-(p-amino-phenyl)-2-amino-ethanols-(1) and salts |
NL176168C (nl) | 1972-12-18 | 1985-03-01 | Thomae Gmbh Dr K | Werkwijze ter bereiding respectievelijk vervaardiging van een farmaceutisch preparaat en werkwijze ter bereiding van daarbij bruikbare nieuwe gesubstitueerde 1-(4-aminofenyl)-2-amino-ethanol-derivaten die, behalve een analgetische, uterusspasmolytische en anti-spastische werking op de dwarsgestreepte spieren, in het bijzonder een beta2-mimetische en/of beta1-blokkerende werking bezitten. |
US3985887A (en) | 1973-10-19 | 1976-10-12 | Smithkline Corporation | 3-Substituted-4-hydroxyphenyl-2-piperidylcarbinols as β-adrenergic stimulants |
US3910933A (en) | 1973-10-19 | 1975-10-07 | Smithkline Corp | 3-Substituted-4-hydroxyphenyl-2-piperidylcarbinols |
JPS539227B2 (pl) | 1973-12-26 | 1978-04-04 | ||
DE2413102C3 (de) | 1974-03-19 | 1980-09-11 | C.H. Boehringer Sohn, 6507 Ingelheim | Verfahren zur Herstellung von l-(3,5-Dihydroxyphenyl)-t-hydroxy-2- eckige Klammer auf 1-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan |
CA1030146A (en) * | 1974-04-18 | 1978-04-25 | American Home Products Corporation | Thiophene ethanolamines |
DE2548053A1 (de) | 1974-10-30 | 1976-05-06 | Scherico Ltd | Azazyklische verbindungen |
US3952101A (en) | 1975-04-14 | 1976-04-20 | Smithkline Corporation | α-Amino methyl-5-hydroxy-2-pyridinemethanols |
CH624395A5 (pl) | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
JPS6048503B2 (ja) | 1976-02-27 | 1985-10-28 | 興和株式会社 | 新規な1−フエニル−2−アミノエタノ−ル誘導体 |
JPS609713B2 (ja) | 1976-10-08 | 1985-03-12 | 大塚製薬株式会社 | カルボスチリル誘導体 |
AR214005A1 (es) | 1977-05-02 | 1979-04-11 | Pfizer | Procedimiento para preparar 2-hidroximetil-3-hidroxi-6-(1-hidroxi-2-t-butilaminoetil)piridina |
NZ187066A (en) | 1977-05-03 | 1981-02-11 | Hoffmann La Roche | 4-(3-substitutedamino-2-hydroxypropoxy)-benzimidazolidin-2-(ones or thiones) |
JPS5852640B2 (ja) | 1977-06-06 | 1983-11-24 | 味の素株式会社 | ペルオキシダ−ゼ活性の測定方法 |
FR2424278A1 (fr) * | 1978-04-24 | 1979-11-23 | Parcor | Procede de preparation de thieno(2,3-c) et thieno(3,2-c)pyridines |
DE2838923A1 (de) | 1978-09-07 | 1980-04-03 | Thomae Gmbh Dr K | Verwendung von phenylaethanolaminen als antiphlogistica |
FR2436779A1 (fr) | 1978-09-22 | 1980-04-18 | Pharmindustrie | Derives de pyrrolidine-2 methanol utilisables comme medicaments |
DE3061334D1 (en) | 1979-06-16 | 1983-01-20 | Beecham Group Plc | Ethanamine derivatives, their preparation and use in pharmaceutical compositions |
FR2460929A1 (fr) | 1979-07-06 | 1981-01-30 | Roussel Uclaf | Nouveaux derives de l'a-phenyl 2-pyrrolidinemethanol et leur sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
JPS5655369A (en) * | 1979-10-12 | 1981-05-15 | Yoshitomi Pharmaceut Ind Ltd | Pyridinemethanol derivative |
JPS5655355A (en) | 1979-10-15 | 1981-05-15 | Paamakemu Asia:Kk | Preparation of alkylenediamine derivative |
FR2486074A1 (fr) | 1979-12-14 | 1982-01-08 | Lafon Labor | Derives de fluorophenacyl-amine, leur procede de preparation et leur application en therapeutique |
EP0043807B1 (en) | 1980-07-09 | 1984-05-30 | Aktiebolaget Draco | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates |
JPS57169450A (en) | 1981-04-13 | 1982-10-19 | Lafon Labor | Fluorophenacyl-amine derivative and application to remedy |
PL144053B1 (en) | 1983-01-31 | 1988-04-30 | Lilly Co Eli | Method of stimulating growth of domesticated animals,improving effectivness of food utilization ba domesticated animals and improving leanness of domesticated animals and fodder pre-mixture |
EP0128120A3 (de) | 1983-06-02 | 1985-11-13 | Ciba-Geigy Ag | Trisubstituierte Oxazolidinone |
ES8502099A1 (es) | 1983-08-02 | 1984-12-16 | Espanola Farma Therapeut | Procedimiento de obtencion de nuevos compuestos derivados de la difenil-metilen-etilamina. |
CA1249992A (en) | 1983-11-10 | 1989-02-14 | Marcel Muller | Oxazolidines |
GB2151612B (en) | 1983-11-25 | 1988-08-03 | Lafon Labor | The use of the family of 2-amino-1-(methoxyphenyl)-1- ethanol derivatives for the manufacture of a medicament for use as a vasodilating agent |
US4614746A (en) | 1985-03-21 | 1986-09-30 | American Cyanamid Company | 5-fluorobenzonitrile derivatives for increasing the lean meat to fat ratio and/or enhancing the growth rate of warm-blooded animals |
DE3514725A1 (de) | 1985-04-24 | 1986-10-30 | Boehringer Ingelheim Vetmedica GmbH, 6507 Ingelheim | Ss(pfeil abwaerts)2(pfeil abwaerts)-mimetica vom typ der 4-amino-phenylaethanolamine zur verhinderung von peptischen magen-geschwueren |
US4863959A (en) | 1985-10-17 | 1989-09-05 | American Cyanamid Company | Anthranilonitrile derivatives as useful agents for promoting growth, improving feed efficiency, and for increasing the lean meat to fat ratio of warm-blooded animals |
ATE61794T1 (de) | 1985-10-17 | 1991-04-15 | American Cyanamid Co | Anthranilonitrilderivate und verwandte verbindungen als nuetzliche stoffe zur wachstumsbeschleunigung, zur verbesserung der futterqualitaet und zur steigerung des fleisch/fett-verhaeltnisses bei warmbluetigen tieren. |
DE3615293A1 (de) * | 1986-05-06 | 1987-11-12 | Bayer Ag | Verwendung von heteroarylethylaminen zur leistungsfoerderung bei tieren, heteroarylethylamine und verfahren zu ihrer herstellung |
GB8714901D0 (en) | 1986-07-23 | 1987-07-29 | Ici Plc | Amide derivatives |
US4814350A (en) | 1986-09-10 | 1989-03-21 | American Cyanamid Company | Method of treating diabetes with 5-[1-hydroxy-2-(isopropylamino)ethyl]anthranilonitrile |
IE60964B1 (en) | 1986-12-11 | 1994-09-07 | Roussel Uclaf | Zootechnical compositions containing a beta-adrenergic |
DK123788A (da) | 1987-03-10 | 1988-09-11 | Beecham Group Plc | Morpholin-derivater |
DE3725084A1 (de) * | 1987-07-29 | 1989-02-09 | Bayer Ag | Substituierte pyridinethanolamine, verfahren zu ihrer herstellung und ihre verwendung als leistungsfoerderer bei tieren |
ATE116284T1 (de) | 1987-08-12 | 1995-01-15 | Sanofi Sa | Verfahren zur o-alkylierung von n- (hydroxy)aralkylphenylethanolamin. |
US5019578A (en) * | 1987-11-27 | 1991-05-28 | Merck & Co., Inc. | β-adrenergic agonists |
NZ226991A (en) * | 1987-11-27 | 1992-03-26 | Merck & Co Inc | Alpha-heterocyclically-substituted ethanolamines and use as animal growth promotors |
FR2647310B1 (fr) | 1989-05-29 | 1992-01-17 | Roussel Uclaf | Utilisation de beta-adrenergiques pour la fabrication de compositions zootechniques |
IE65511B1 (en) | 1989-12-29 | 1995-11-01 | Sanofi Sa | New phenylethanolaminomethyltetralins |
ES2085468T3 (es) | 1990-01-05 | 1996-06-01 | Sepracor Inc | Albuterol r(-) opticamente puro para tratar el asma. |
US5061727A (en) | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
GB9107196D0 (en) | 1991-04-05 | 1991-05-22 | Sandoz Ag | Improvements in or relating to organic compounds |
NO179246C (no) | 1991-11-20 | 1996-09-04 | Sankyo Co | Aromatiske amino-alkoholderivater og mellomprodukter til fremstilling derav |
IL104567A (en) | 1992-02-03 | 1997-03-18 | Fujisawa Pharmaceutical Co | Ethanolamine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
US5451677A (en) | 1993-02-09 | 1995-09-19 | Merck & Co., Inc. | Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity |
US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
US5705515A (en) | 1994-04-26 | 1998-01-06 | Merck & Co., Inc. | Substituted sulfonamides as selective β-3 agonists for the treatment of diabetes and obesity |
US5726165A (en) | 1994-07-29 | 1998-03-10 | Smithkline Beecham P.L.C. | Derivatives of 4-(2-aminoethyl)phenoxymethyl-phosphonic and -phosphinic acid and pharmaceutical and veterinary uses therefor |
US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
US6037362A (en) | 1996-01-10 | 2000-03-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Tricyclic compounds and drug compositions containing the same |
WO1998022480A1 (en) | 1996-11-18 | 1998-05-28 | Smithkline Beecham Plc | Phosphorus containing aryloxy or arylthio propanolamine derivatives |
EP0968209A1 (en) | 1997-01-28 | 2000-01-05 | Merck & Co., Inc. | THIAZOLE BENZENESULFONAMIDES AS $g(b) 3? AGONISTS FOR THE TREATMENT OF DIABETES AND OBESITY |
JP3193706B2 (ja) | 1997-10-17 | 2001-07-30 | 山之内製薬株式会社 | アミド誘導体又はその塩 |
AU2223899A (en) | 1998-01-12 | 1999-07-26 | Georgetown University Medical Center | G protein-related kinase mutants in essential hypertension |
AU2781899A (en) | 1998-02-24 | 1999-09-15 | Trustees Of The University Of Pennsylvania, The | Use of a cardiac purinoceptor to effect cellular glucose uptake |
GB9812709D0 (en) | 1998-06-13 | 1998-08-12 | Glaxo Group Ltd | Chemical compounds |
CN1161018C (zh) | 1998-06-18 | 2004-08-11 | 诺瓦提斯公司 | 防治害虫的组合物 |
ES2182543T3 (es) | 1998-06-18 | 2003-03-01 | Novartis Ag | Composicion para ahuyentar parasitos. |
MY126489A (en) | 1998-07-08 | 2006-10-31 | Kissei Pharmaceutical | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
US20030018061A1 (en) | 2000-01-28 | 2003-01-23 | Kohei Ogawa | Novel remedies with the use of beta 3 agonist |
US6403612B2 (en) | 2000-01-31 | 2002-06-11 | Merck & Co., Inc. | Thrombin receptor antagonists |
AU5257401A (en) | 2000-04-28 | 2001-11-12 | Asahi Chemical Ind | Novel bicyclic compounds |
CA2423792A1 (en) | 2000-10-20 | 2002-04-25 | Pfizer Products Inc. | Alpha-aryl ethanolamines and their use as beta-3 adrenergic receptor agonists |
US20100022658A1 (en) | 2000-11-01 | 2010-01-28 | Cognition Pharmaceuticals Llc | Methods for treating cognitive impairment in humans |
AU782148B2 (en) | 2001-03-29 | 2005-07-07 | Molecular Design International, Inc. | Beta3-adrenoreceptor agonists, agonist compositions and methods of making and using the same |
CN1276911C (zh) | 2001-09-30 | 2006-09-27 | 沈阳药科大学 | 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 |
WO2003032969A2 (en) | 2001-10-15 | 2003-04-24 | National Research Council Of Canada | Anti-glycation agents for preventing age-, diabetes-, and smoking-related complications |
JP2005533771A (ja) | 2002-06-04 | 2005-11-10 | ファイザー・プロダクツ・インク | ジペプチジルペプチダーゼiv阻害剤としてのフッ素化環式アミド |
EP1540332A1 (en) | 2002-07-03 | 2005-06-15 | Duke University | Methods of screening compounds for grk6 modulating activity |
US6831081B2 (en) | 2002-09-04 | 2004-12-14 | Pharmacia & Upjohn | 4-Oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents |
AU2003286776A1 (en) | 2002-10-30 | 2004-06-07 | Guilford Pharmaceuticals Inc. | Novel inhibitors of dipeptidyl peptidase iv |
US7550133B2 (en) | 2002-11-26 | 2009-06-23 | Alexza Pharmaceuticals, Inc. | Respiratory drug condensation aerosols and methods of making and using them |
GB0303396D0 (en) | 2003-02-14 | 2003-03-19 | Glaxo Group Ltd | Medicinal compounds |
WO2004085414A1 (en) | 2003-03-26 | 2004-10-07 | Pharmacia & Upjohn Company Llc | Process to produce enantiomerically enriched 1-aryl- and 1-heteroaryl-2-aminoethanols |
US20070099884A1 (en) | 2003-06-06 | 2007-05-03 | Erondu Ngozi E | Combination therapy for the treatment of diabetes |
AU2003904237A0 (en) | 2003-08-08 | 2003-08-21 | Garvan Institute Of Medical Research | Novel translocation assay |
CA2538415A1 (en) | 2003-09-15 | 2005-03-24 | Wilfred Wayne Lautt | Use of antagonists of hepatic sympathetic nerve activity |
JP2005097149A (ja) | 2003-09-24 | 2005-04-14 | Dainippon Pharmaceut Co Ltd | [3−[(2r)−[[(2r)−(3−クロロフェニル)−2−ヒドロキシエチル]アミノ]プロピル]−1h−インドール−7−イルオキシ]酢酸の溶媒和物 |
FR2861073B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
CA2554959A1 (en) | 2004-01-29 | 2005-08-11 | Neuromolecular, Inc. | Combination of a nmda receptor antagonist and a mao-inhibitor or a gadpf-inhibitor for the treatment of central nervous system-related conditions |
HUP0400405A3 (en) | 2004-02-10 | 2009-03-30 | Sanofi Synthelabo | Pyrimidine derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
DE102004019539A1 (de) | 2004-04-22 | 2005-11-10 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittel zur Behandlung von Atemwegserkrankungen |
US20050250944A1 (en) * | 2004-05-04 | 2005-11-10 | Jian Chen | Synthesis and uses of synephrine derivatives |
EP1595873A1 (de) | 2004-05-13 | 2005-11-16 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Cycloalkylderivate zur Behandlung von Atemswegerkrankungen |
WO2005110990A1 (de) | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Hydroxy-substituierte benzkondensierte heterozyklen als betaagonisten zur behandlung von atemwegserkrankungen |
WO2005114195A1 (en) | 2004-05-21 | 2005-12-01 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g protein-coupled receptor kinase 4 (grk4) |
KR20070027747A (ko) | 2004-06-30 | 2007-03-09 | 콤비네이토릭스, 인코포레이티드 | 대사 질환의 치료 방법 및 시약 |
BRPI0513262A (pt) | 2004-07-12 | 2008-04-29 | Bayer Cropscience Ag | heterociclos substituìdos |
EP1786410A2 (en) | 2004-09-07 | 2007-05-23 | Sosei R&D Ltd. | The treatment of inflammatory disorders and pain |
US20100173928A1 (en) | 2005-01-28 | 2010-07-08 | Sabatini David M | Phosphorylation and regulation of AKT/PKB by the rictor-mTOR complex |
ES2348920T3 (es) * | 2005-04-13 | 2010-12-17 | Astion Development A/S | Agonistas de adrenoceptores beta-2 para el tratamiento de enfermedades del tejido conectivo de la piel. |
ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
TW200740779A (en) | 2005-07-22 | 2007-11-01 | Mitsubishi Pharma Corp | Intermediate compound for synthesizing pharmaceutical agent and production method thereof |
CN101252952A (zh) | 2005-08-29 | 2008-08-27 | 橘生药品工业株式会社 | 用于由泪液减少所引起的疾病的预防或治疗剂 |
US8293900B2 (en) | 2005-09-29 | 2012-10-23 | Merck Sharp & Dohme Corp | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
JP2007217368A (ja) | 2006-02-17 | 2007-08-30 | Japan Health Science Foundation | PGC−1α発現促進剤及びPGC−1α発現抑制剤、並びにそれらの使用方法 |
EP1829534A1 (en) | 2006-03-02 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | Use of compounds binding to the sigma receptor for the treatment of metabolic syndrome |
EP1991211A1 (en) | 2006-02-28 | 2008-11-19 | Laboratorios Del Dr. Esteve, S.A. | Use of compounds binding to the sigma receptor for the treatment of metabolic syndrome |
GB0604826D0 (en) | 2006-03-09 | 2006-04-19 | Arakis Ltd | The treatment of inflammatory disorders and pain |
JP2009531334A (ja) | 2006-03-24 | 2009-09-03 | ナショナル リサーチ カウンセル オブ カナダ | 抗糖尿病性白内障化合物及びそれらの用途 |
CA2659155A1 (en) | 2006-07-20 | 2008-01-24 | Amgen Inc. | Substituted azole aromatic heterocycles as inhibitors of 11.beta.-hsd-1 |
CA2660707C (en) | 2006-08-10 | 2014-07-08 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Preparation of (r,r)-fenoterol and (r,r)- or (r,s)-fenoterol analogues and their use in treating congestive heart failure |
KR100821567B1 (ko) | 2006-11-01 | 2008-04-15 | 한국화학연구원 | 광학 활성 2-설포닐옥시-1-페닐에탄올 유도체의 제조방법 |
GB0624757D0 (en) | 2006-12-12 | 2007-01-17 | Sosei R & D Ltd | Novel compounds |
FR2917735B1 (fr) | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
PE20091825A1 (es) | 2008-04-04 | 2009-12-04 | Merck & Co Inc | Hidroximetil pirrolidinas como agonistas del receptor adrenergico beta 3 |
CA2638573C (en) | 2008-04-30 | 2013-03-12 | Universiteit Gent | Substituted 7-azabicyclo[2.2.1]heptyl derivatives useful for making pharmaceutical compositions |
US8389561B2 (en) | 2008-04-30 | 2013-03-05 | Universiteit Gent | Substituted 7-azabicyclo[2.2.1]heptyl derivatives useful for making pharmaceutical compositions |
FR2932818B1 (fr) | 2008-06-23 | 2015-12-04 | Centre Nat Rech Scient | Lignee d'adipocytes bruns humains et procede de differenciation a partir d'une lignee de cellules hmads. |
WO2010016939A1 (en) | 2008-08-08 | 2010-02-11 | The Trustees Of Columbia University In The City Of New York | Hypoglycemic dihydropyridones |
US8637524B2 (en) | 2009-07-28 | 2014-01-28 | Auspex Pharmaceuticals, Inc | Pyrimidinone inhibitors of lipoprotein-associated phospholipase A2 |
US20110055367A1 (en) | 2009-08-28 | 2011-03-03 | Dollar James E | Serial port forwarding over secure shell for secure remote management of networked devices |
EP2480077B1 (en) | 2009-09-22 | 2015-02-18 | Merck Sharp & Dohme Corp. | Pyrrolidines as glucagon receptor antagonists, compositions, and methods for their use |
AU2011224241B2 (en) | 2010-03-10 | 2014-05-08 | Sri International | The use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas |
JP2013522302A (ja) | 2010-03-14 | 2013-06-13 | グローブイミューン,インコーポレイテッド | 酵母系免疫療法を使用した感染症の薬理ゲノミクス及び治療反応性ガイド治療 |
EP2426202A1 (en) | 2010-09-03 | 2012-03-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Kinases as targets for anti-diabetic therapy |
US20120122843A1 (en) * | 2010-11-11 | 2012-05-17 | Astrazeneca Ab | Compounds and Their Use for Treatment of Amyloid Beta-Related Diseases |
US9034839B2 (en) | 2012-04-20 | 2015-05-19 | Aptamir Therapeutics, Inc. | miRNA modulators of thermogenesis |
US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
US9657348B2 (en) | 2013-01-13 | 2017-05-23 | Atrogi Ab | Method of screening compounds for the treatment of diabetes |
CN103565784A (zh) | 2013-11-04 | 2014-02-12 | 匡仲平 | 一种减肥药剂 |
US9891212B2 (en) | 2013-12-16 | 2018-02-13 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
TWI659019B (zh) * | 2014-02-28 | 2019-05-11 | 日商帝人製藥股份有限公司 | 吡唑醯胺衍生物 |
WO2016004995A1 (en) | 2014-07-09 | 2016-01-14 | Atrogi Ab | A method of screening for a compound capable of stimulating glucose transport into brown and/or brite adipocytes of a mammal, a kit for use in such a method |
CN105078946A (zh) | 2015-08-07 | 2015-11-25 | 重庆理工大学 | 沙美特罗在治疗二型糖尿病、胰岛素抵抗药物上的应用 |
WO2017153737A1 (en) * | 2016-03-07 | 2017-09-14 | Atrogi Ab | Compounds for the treatment of hyperglycaemia |
CN106083837B (zh) | 2016-05-27 | 2018-08-31 | 浙江普洛得邦制药有限公司 | 一种噁唑烷酮类抗菌药物及其中间体的制备方法 |
GB201612165D0 (en) | 2016-07-13 | 2016-08-24 | Atrogi Ab | Combinations for the treatment of type 2 diabetes |
GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201903827D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
JP2022527769A (ja) | 2019-03-27 | 2022-06-06 | キュラセン セラピューティクス インコーポレイテッド | ベータアドレナリンアゴニスト及びそれを使用する方法 |
CA3144093A1 (en) | 2019-07-01 | 2021-01-07 | Curasen Therapeutics, Inc. | Beta adrenergic agonist and methods of using the same |
GB202015044D0 (en) | 2020-09-23 | 2020-11-04 | Atrogi Ab | New compounds and methods |
GB202015035D0 (en) | 2020-09-23 | 2020-11-04 | Atrogi Ab | New compounds and methods |
-
2017
- 2017-09-13 GB GBGB1714745.5A patent/GB201714745D0/en not_active Ceased
-
2018
- 2018-09-13 HU HUE18773826A patent/HUE057426T2/hu unknown
- 2018-09-13 EP EP21201891.5A patent/EP3971168A1/en active Pending
- 2018-09-13 RU RU2020108523A patent/RU2020108523A/ru unknown
- 2018-09-13 HR HRP20220177TT patent/HRP20220177T1/hr unknown
- 2018-09-13 MX MX2020002825A patent/MX2020002825A/es unknown
- 2018-09-13 EP EP18773826.5A patent/EP3681872B1/en active Active
- 2018-09-13 SI SI201830560T patent/SI3681872T1/sl unknown
- 2018-09-13 ES ES18773826T patent/ES2902073T3/es active Active
- 2018-09-13 PT PT187738265T patent/PT3681872T/pt unknown
- 2018-09-13 KR KR1020207010465A patent/KR20200052936A/ko not_active Application Discontinuation
- 2018-09-13 WO PCT/GB2018/052595 patent/WO2019053427A1/en unknown
- 2018-09-13 PL PL18773826T patent/PL3681872T3/pl unknown
- 2018-09-13 US US16/645,286 patent/US11357757B2/en active Active
- 2018-09-13 CN CN201880072013.6A patent/CN111315726A/zh active Pending
- 2018-09-13 JP JP2020514503A patent/JP7358338B2/ja active Active
- 2018-09-13 RS RS20220113A patent/RS62895B1/sr unknown
- 2018-09-13 AU AU2018332501A patent/AU2018332501B2/en active Active
- 2018-09-13 CA CA3075707A patent/CA3075707A1/en active Pending
- 2018-09-13 BR BR112020005113-6A patent/BR112020005113A2/pt unknown
- 2018-09-13 KR KR1020237043200A patent/KR20230175328A/ko not_active Application Discontinuation
- 2018-09-13 LT LTEPPCT/GB2018/052595T patent/LT3681872T/lt unknown
-
2020
- 2020-03-09 IL IL273180A patent/IL273180A/en unknown
- 2020-03-12 MX MX2023011675A patent/MX2023011675A/es unknown
-
2022
- 2022-01-13 US US17/575,175 patent/US12036210B2/en active Active
- 2022-02-16 CY CY20221100138T patent/CY1125004T1/el unknown
-
2023
- 2023-09-27 JP JP2023165207A patent/JP2023182659A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP7358338B2 (ja) | 2023-10-10 |
HUE057426T2 (hu) | 2022-05-28 |
US20220133703A1 (en) | 2022-05-05 |
RU2020108523A (ru) | 2021-10-15 |
AU2018332501A1 (en) | 2020-04-23 |
JP2023182659A (ja) | 2023-12-26 |
RU2020108523A3 (pl) | 2022-03-23 |
US20210030731A1 (en) | 2021-02-04 |
SI3681872T1 (sl) | 2022-04-29 |
KR20230175328A (ko) | 2023-12-29 |
MX2020002825A (es) | 2020-09-14 |
US12036210B2 (en) | 2024-07-16 |
AU2018332501B2 (en) | 2023-09-21 |
ES2902073T3 (es) | 2022-03-24 |
EP3681872A1 (en) | 2020-07-22 |
CA3075707A1 (en) | 2019-03-21 |
EP3681872B1 (en) | 2021-11-17 |
IL273180A (en) | 2020-04-30 |
HRP20220177T1 (hr) | 2022-04-29 |
EP3971168A1 (en) | 2022-03-23 |
CN111315726A (zh) | 2020-06-19 |
LT3681872T (lt) | 2022-01-25 |
US11357757B2 (en) | 2022-06-14 |
CY1125004T1 (el) | 2023-01-05 |
RS62895B1 (sr) | 2022-03-31 |
BR112020005113A2 (pt) | 2020-09-15 |
PT3681872T (pt) | 2021-12-22 |
JP2020534263A (ja) | 2020-11-26 |
WO2019053427A1 (en) | 2019-03-21 |
PL3681872T3 (pl) | 2022-04-04 |
GB201714745D0 (en) | 2017-10-25 |
MX2023011675A (es) | 2023-10-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20200052936A (ko) | 과혈당증의 치료에 사용하기 위한 헤테로아릴 치환된 베타-히드록시에틸아민 | |
KR20200051777A (ko) | 플루오로페닐 베타-히드록시에틸아민 및 과혈당증의 치료에서의 이의 용도 | |
KR20200051776A (ko) | 베타-히드록시 헤테로사이클릭 아민 및 과혈당증의 치료에서의 이의 용도 | |
KR20210141622A (ko) | 과혈당증의 치료에 유용한 헤테로시클릴(페닐)메탄올 화합물 | |
KR20220002903A (ko) | 과혈당증의 치료에 유용한 헤테로아릴(헤테로시클릴)메탄올 화합물 | |
JP2019510082A (ja) | 高血糖症の治療のための化合物 | |
KR20200052937A (ko) | 카이랄 베타-히드록시에틸아민 및 과혈당증의 치료에서의 이의 용도 | |
RU2801096C2 (ru) | Фторфенил-бета-гидроксиэтиламины и их применение для лечения гипергликемии | |
WO2024200777A1 (en) | Substituted hydroxymethyl pyrrolidines for use in the treatment of hyperglycaemia and disorders characterised by hyperglycaemia |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
E902 | Notification of reason for refusal | ||
AMND | Amendment | ||
E601 | Decision to refuse application | ||
X091 | Application refused [patent] | ||
E902 | Notification of reason for refusal | ||
E902 | Notification of reason for refusal |